Connect public, paid and private patent data with Google Patents Public Datasets

Optically active compound having a plurality of asymmetric carbon atoms

Download PDF

Info

Publication number
US4973426A
US4973426A US07160279 US16027988A US4973426A US 4973426 A US4973426 A US 4973426A US 07160279 US07160279 US 07160279 US 16027988 A US16027988 A US 16027988A US 4973426 A US4973426 A US 4973426A
Authority
US
Grant status
Grant
Patent type
Prior art keywords
sub
compound
group
represents
liquid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US07160279
Inventor
Kouji Ohno
Shinichi Saito
Hiromichi Inoue
Kazutoshi Miyazawa
Makoto Ushioda
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JNC Corp
Original Assignee
JNC Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Grant date

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28Radicals substituted by singly-bound oxygen or sulfur atoms
    • C07D213/30Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D237/00Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/14Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/34One oxygen atom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/52Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/58Dopants or charge transfer agents
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/52Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/58Dopants or charge transfer agents
    • C09K19/586Optically active dopants; chiral dopants
    • C09K19/588Heterocyclic compounds

Abstract

An optically active compound having particularly a specific feature of increasing spontaneous polarization value as one of important specific features for ferroelectric liquid crystal compositions, and a ferroelectric liquid crystal composition containing the compound are provided, which compound is expressed by the formula ##STR1## wherein R1 represents a linear or branched chain alkyl, alkoxy, alkanoyl, alkoxycarbonyl or alkoxycarbonyloxy each of 1 -15C, H, halogen or -CN; R2 represents an optically active group having 2-20 skeletal atoms, ##STR2## wherein X represents H, halogen or -CN; l represents an integer of 1-10; m is 0 or 1; and * indicates asymmetric C.

Description

BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention relates to a novel organic compound and a liquid crystal composition containing the same. More particularly it relates to an organic compound having an optically active group and being useful as a component of ferroelectric liquid crystal compositions, and a ferroelectric liquid crystal composition containing the same.

2. Description of the Related Art

At present, TN (twisted nematic) display mode has been most broadly used as liquid crystal display elements and this TN liquid crystal display has a number of advantages such as low driving voltage, small power consumption, etc. However, it is inferior in the aspect of the response rate to emissive mode display elements such as cathode ray tube, electroluminescence, plasma display, etc. Further, a novel TN mode display element having its twist angle enlarged up to 180°-270° has also been developed, but it is still inferior in the aspect of the response rate As described above, efforts of various improvements have so far been made, but those having fully satisfactory performances have not yet been obtained. However, a novel display mode utilizing ferroelectric liquid crystals, the research of which has recently been extensively made, has a possibility of notably improving the response rate (Clark et al; Applied Phys. lett., 36, 899 (1980)). This mode utilizes chiral smectic phases such as chiral smectic C phase (hereinafter abbreviated to SC*). It is known that the phases exhibiting ferroelectric properties are not only limited to SC* phase, but phases of chiral smectic F, G, H, I, etc. also exhibit ferroelectric properties.

A number of specific features are required for ferroelectric liquid crystal materials to be practically used for ferroelectric liquid crystal display elements, but at present, there is no single compound which satisfies the requirements; hence it is necessary to use ferroelectric liquid crystal compositions obtained by mixing some liquid crystal compounds or non-liquid crystal compounds therewith.

SUMMARY OF THE INVENTION

The present inventors have found a compound having a specific feature of enhancing the spontaneous polarization value Ps as one of important specific features necessary for ferroelectric liquid crystal compositions.

The present invention resides in an optically active compound expressed by the formula ##STR3## wherein R1 represents a linear or branched chain alkyl group, alkoxy group, alkanoyl group, alkanoyloxy group, alkoxycarbonyl group or alkoxycarbonyloxy group each of 1 to 15 carbon atoms, hydrogen atom, a halogen atom or cyano group; R2 represents an optically active group having 2 to 20 skeletal atoms in its chain; ##STR4## wherein X represents hydrogen atom, a halogen atom or cyano group; l represents an integer of 1 to 10; m represents 0 or 1; and * indicates an asymmetric carbon atom, and a chiral liquid crystal composition containing the compound.

DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS

In the above formula (I), R1 is preferably a linear chain alkyl group or alkoxy group each of 4 to 14 carbon atoms.

Representative examples of the optically active group R2 are an optically active monohalogenated alkyl group or an alkyl group having an alkoxy branch each of 2 to 20 carbon atoms. Examples of the monohalogenated alkyl group are ##STR5##

In these formulas, X represents F, Cl or Br; and R3 represents a linear or branched chain alkyl group each of 1 to 15 carbon atoms and when R3 represents a branched chain alkyl group, it may be an optically active group. Preferred examples of R2 wherein R3 represents a linear chain alkyl group and X represents a halogen atom are ##STR6##

Further, preferred examples of R2 wherein R3 represents an optically active alkyl group and X represents a halogen atom are ##STR7##

Further, preferred examples of R2 in the case of an alkyl group having an alkoxy branch are ##STR8## wherein R3 is as defined above and R4 represents a linear or branched chain alkyl group each of 1 to 10 carbon atoms and when R4 represents a branched chain alkyl group, R4 may be an optically active group. Preferred examples of R2 wherein R3 and R4 are both a linear chain alkyl group are ##STR9##

Preferred examples of R2 wherein R4 represents an optically active alkyl group are ##STR10##

Preferred examples of R2 wherein R3 represents an optically active alkyl group and R4 represents a linear chain alkyl group are ##STR11## etc.

Preferred examples of R2 wherein R3 and R4 both represent an optically active alkyl group are ##STR12##

Further, preferred examples of ##STR13## are ##STR14##

Among these, more preferred examples are ##STR15##

The specific feature of the compound expressed by the formula (I) of the present invention consists in that the compound has a large spontaneous polarization value (Ps) or potential spontaneous polarization value.

According to the measurement of the present inventors, for example when the Ps value of the compound of Example 1 mentioned below, ##STR16## was measured by a extrapolation method, it amounted to 94 nC/cm2 at 25° C. Since this value was not obtained by measuring the compound itself, it cannot be said that this value is the Ps of the compound itself, but in the case of practical use, compounds having such an effectiveness are very useful.

On the other hand, the Ps of a compound disclosed in Japanese patent application No. Sho 61-133269, the invention of which has also been made by the present inventors, and expressed by the formula ##STR17## was measured to give 57 nC/cm2 at 25° C. The Ps value of the compound (A) having the linear chain acyl group of the compound (B) converted into an optically active substituent acyl group became about twice that of the compound (B). Namely, when one more asymmetric carbon atom was introduced into the compound (B), the Ps value was notably increased. Thereby a ferroelectric composition containing the compound of the formula (I) of the present invention in an amount of 10% by weight can realize a response time as short as 100 μsec at 25° C.

Further, when the compound of the formula (I) of the present invention in a suitable quantity is added to a chiral or achiral smectic liquid crystal compound or a chiral smectic liquid crystal composition, it is possible to notably increase their Ps values.

The absolute configurations of the respective asymmetric carbon atoms in the formula (I) may be either of (R)-configuration or (S)-configuration.

When the compound of the present invention is added to a nematic liquid crystal composition, the resulting chiral nematic liquid crystal composition has a very short chiral pitch as illustrated in the Examples; hence the compound can be said to be very useful as a pitch-adjusting agent for chiral nematic liquid crystal compositions. Further, its temperature-dependency δP is small as illustrated in the Examples. The δP of (S)-4-(2'-methylbutyl)-4'-cyanobiphenyl as one of currently known pitch-adjusting agents is 0.543 under the same conditions; hence, even as compared therewith, it is seen that the δP of the compound of the present invention is small. In the case of the so-called super TN mode display having the twist angle enlarged up to 180°-270°, since a large temperature-dependency of pitch notably reduces its display quality, the temperature-dependency of pitch is preferred to be smaller. When a chiral nematic liquid crystal composition obtained by adding the compound of the present invention is used for a super TN mode display, the temperature-dependency of pitch is small; hence it is possible to prepare a superior super TN mode element having a small reduction in the display quality.

The compound of the formula (I) may be prepared for example through the following route: ##STR18##

Using various combinations of compounds corresponding to the compound (1) with compounds corresponding to the compound (5), various compounds of the formula (I) may be obtained.

The compound and liquid crystal composition of the present invention will be described in more detail by way of the following Examples.

EXAMPLE 1 Preparation of (2'S, 2"S)-4'-octyloxy-4-(2'-(2"-butoxypropionyloxy)-propoxy)biphenyl (a compound of the formula (I) wherein R1 =octyloxy group; ##STR19##

(i) Preparation of (S)-1-(4'-octyloxy-4-biphenyloxy)propan-2-ol

A mixture of (2S)-2-tetrahydropyranyloxy-1-hydroxypropane(137 g, 0.85 mol) prepared according to the literature (C. Malanga et al, Synthetic Communications, 12 (1), 67-70 (1982)) with anhydrous pyridine (600 g) was cooled with ice, followed by dropwise adding to the mixture, a solution of p-toluenesulfonyl chloride (165 g, 0.87 mol) in pyridine (200 ml), agitating the mixture at 0° C. for 2 hours, successively agitating it at room temperature for 2 hours, allowing it to stand overnight, adding toluene (1 l), further adding 2N-NOH aqueous solution (500 ml), separating the resulting organic layer, several times washing it with water to make it neutral, drying it over MgSO4 and distilling off the solvent, to obtain (2S)-2-(2'-tetrahydropyranyloxy)-1-(p-toluenesulfonyloxy)-propane (257 g; yield 95.9%).

A solution of (2S)-2-(2'-tetrahydropyranyloxy)-1-(p-toluenesulfonyloxy)-propane (20 g) in N,N-dimethylformamide (hereinafter abbreviated to DMF) (300 ml) was added to a mixture of sodium hydride (60%) (2 g), 4-hydroxy-4'-octyloxy-biphenyl(10 g) and tetrahydrofuran (hereinafter abbreviated to THF) (200 ml), followed by agitating the resulting mixture at 60° C. for 4 hours, allowing it to cool down to room temperature, adding toluene (300 ml) and water (300 ml), separating the resulting organic layer, washing it with an alkali solution and then with water, concentrating it, adding ethanol (300 ml) and pyridium p-toluenesulfonate (hereinafter abbreviated to PPTS) (2 g), agitating the mixture at 50° C. for 3 hours, distilling off ethanol, adding toluene (300 ml), washing the resulting organic layer with water, concentrating it and recrystallizing the concentrate, to obtain (S)-1-(4'-octyloxy-4-biphenylyloxy)-propan-2-ol (8 g).

(ii) Preparation of (S)-2-butoxypropionic acid

Silver oxide (77.5 g, 0.3 mol) was added to a mixture of (S)-(+)-ethyl lactate (49.4 g, 0.4 mol) with 1-iodobutane (100 g, 0.5 mol) over 2 hours, followed by allowing the mixture to stand at room temperature for 3 days, adding ether (30 ml) for dilution, filtering the resulting mixture, distilling off ether, washing the residue with 2N-NaOH aqueous solution, drying it over anhydrous MgSO4 and distilling under reduced pressure, to obtain (S)-ethyl 2-butoxypropionate (30.7 g, b.p. 64° C./7 mmHg), adding thereto 5N-NaOH aqueous solution (50 ml), agitating the mixture at room temperature for 5 hours, pouring it in 6N-hydrochloric acid (75 ml) to extract the resulting organic layer with ether, washing the resulting organic layer with water and distilling off ether, to obtain (S)-2-butoxypropionic acid (21. 4 g).

Further, using (R)-methyl lactate as raw material, (R)-2-butoxypropionic acid was similarly obtained.

(iii) Preparation of the objective compound

To dichloromethane (500 ml) were added N,N-dicyclohexylcarbodiimide (hereinafter abbreviated to DCC) (13.0 g, 0.05 mol), 4-N,N'-dimethylaminopyridine (hereinafter abbreviated to DMAP) (2.0 g), (S)-1-(4'-octyloxy-4-biphenyloxy)-propan-2-ol (13.0 g) obtained in (i) and (S)-2-butoxypropionic acid (2.0 g) obtained in (ii), followed by agitating the mixture at room temperature for 5 hours, filtering off deposited crystals, washing the filtrate with 6N-hydrochloric acid, then with 2N-NaOH aqueous solution and further with water until the washing water became neutral, distilling off dichloromethane and recrystallizing the residue from ethanol, to obtain (2'S, 2"S)-4'-octyloxy-4-(2'-(2"-butoxypropionyloxy)-propoxy)biphenyl (8.0 g, m.p. 50.0° C.).

The above process was repeated except that (S)-(+)-ethyl lactate was replaced by (R)-(-)-ethyl lactate to obtain (2'S, 2"R)-4'-octyloxy-4-(2'(2"-butoxypropionyloxy)-propoxy)biphenyl (m.p. 41.0° C.).

EXAMPLE 2 Preparation of 4'-octyloxy-4-(2'-(2"-chloro-3"-methylvaleryloxy)-propoxy)biphenyl (a compound of the formula (I) wherein R1 =octyloxy group; ##STR20## l=1; m=0; and ##STR21##

(i) Preparation of (2S,3S)-2-chloro-3-methylvaleric acid

L-isoleucine (105 g) was added to 6N-hydrochloric acid (1 l), followed by agitating the mixture, cooling it with ice, adding sodium nitrite (80 g), agitating the mixture at 0° C. for 3 hours, adding ether (300 ml), separating the resulting organic layer, extracting the aqueous layer with ether (150 ml), combining the organic layers, drying over MgSO4, distilling off ether and distilling the residue under reduced pressure, to obtain (2S,3S)-2-chloro-3-methylvaleric acid (34.2 g, b.p. 96-97/4 mmHg).

(ii) Preparation of the objective compound

In dichloromethane (300 ml) were dissolved (S)-1-(4'-octyloxy-4-biphenylyl)-propan-2-ol (8.0 g), DCC (15.0 g) and DMAP (2.0 g), followed by adding to the solution, (2S,3S)-2-chloro-3-methylvaleric acid (9.0 g) obtained in the above (i), agitating the mixture at room temperature for 6 hours, filtering off deposited crystals, washing the resulting organic layer with 6N-hydrochloric acid, washing the organic layer with water until the washing water became neutral, distilling off the organic layer and recrystallizing the residue from ethanol to obtain the objective 4'-octyloxy-4-(2'-(2"-chloro-3"-methylvalerylyloxy)-propoxy)biphenyl (4.0 g, m.p. 69.7° C.).

EXAMPLE 3 Preparation of 4'-octyloxy-4-(2'-(2"-propoxypropionyloxy)-propoxy)biphenyl (a compound of the formula (I) wherein R1 =octyloxy group; ##STR22## l=1; m=0; and ##STR23##

(i) Preparation of 2-propoxypropionic acid

Silver oxide (87.5 g, 0.38 mol) was added to a mixture of (R)-methyl lactate (52.1 g, 0.5 mol) with 1-iodopropane (100 g, 0.59 mol) over 3 hours, followed by allowing the mixture to stand at room temperature for 4 days, adding ether (200 ml) for dilution, filtering the mixture, distilling off ether, washing the residue with 2N-NaOH aqueous solution, drying over anhydrous sodium sulfate, distilling it under reduced pressure to obtain (R)-methyl 2-propoxypropionate (46.1 g, b.p. 33°-34° C./5 mmHg). To this (R)-methyl 2-propoxypropionate (28.2 g) were added water (60 ml) and NaOH (10 g), followed by agitating the mixture at room temperature for 3 hours, pouring the mixture in 6N-hydrochloric acid (80 ml), extracting the resulting organic layer with ether, washing the resulting organic layer with water and distilling off ether to obtain 2-propoxypropionic acid (18.0 g).

(ii) Preparation of the objective compound

To dichloromethane (500 ml) were added DCC (13.0 g, 0.06 mol), DMAP (2.0 g) and (S)-1-(4'-octyloxy-4-biphenylyloxy)-propan-2-ol (7.0 g), followed by adding to the mixture, 2'-propoxypropionic acid (7.0g) obtained in (i), agitating the mixture at room temperature for 4 hours, filtering off deposited crystals, washing the filtrate with 6N-hydrochloric acid, then with 2N-NaOH aqueous solution and further with water until the washing water became neutral, distilling off dichloromethane and recrystallizing the residue from ethanol, to obtain the objective compound, i.e.,4'-octyloxy-4-(2'-(2"-propoxypropionyloxy)-propoxy)biphenyl (1.5 g, m.p. 52.0° C.).

EXAMPLE 4 Preparation of 5-nonyl-2-(4'-(2"-(2"'-propoxypropionyloxy)-propoxy)phenyl)pyridine (a compound of the formula (I) wherein R1 =nonyl group; ##STR24## l=1; m=0; and R2 represents ##STR25##

(S)-5-nonyl-2-(4'-(2"-hydroxypropoxy)phenyl)pyridine (m.p. 77.6°-80.3° C.) was reacted with 2-propoxypropionic acid prepared in Example 3 in the same manner as in Example 3 to obtain 5-nonyl-2-(4'-(2"-(2"'-propoxypropionyloxy)-propoxy)phenyl)pyridine (m.p. 58.0° C.).

The physical properties (m.p.) of compounds of Examples 1 to 4 and other compounds of the formula (I) similarly obtained are collectively shown in Table 1.

                                  TABLE 1__________________________________________________________________________In formula (I) Sample No.  R.sup.1        ##STR26##     l                        m                          R.sup.2     configurationAbsolute                                             (°C.)M.P.                                                Note__________________________________________________________________________1     C.sub.8 H.sub.17 O        ##STR27##    1 0                          ##STR28##  S,R    40.52     C.sub.6 H.sub.13 O        ##STR29##    1 0                          ##STR30##  S,R    43.83     C.sub.8 H.sub.17 O        ##STR31##    1 0                          ##STR32##  S,S    52.3                                               Example 34     C.sub.8 H.sub.17 O        ##STR33##    1 0                          ##STR34##  S,R    52.05     C.sub.8 H.sub.17        ##STR35##    1 0                          ##STR36##  S,S    25.86     C.sub.8 H.sub.17 O        ##STR37##    1 0                          ##STR38##  S,S    50.0                                               Example 17     C.sub.8 H.sub.17 O        ##STR39##    1 0                          ##STR40##  S,R    41.0                                               Example 18     C.sub.11 H.sub.23 O        ##STR41##    1 0                          ##STR42##  S,S    57.69     C.sub.10 H.sub.21 O        ##STR43##    1 0                          ##STR44##  S,S    50.210    C.sub.8 H.sub.17 O        ##STR45##    1 0                          ##STR46##  S,S,S  69.7                                               Example 211    C.sub.8 H.sub.17 O        ##STR47##    1 1                          ##STR48##  R,R    42.612    C.sub.8 H.sub.17 O        ##STR49##    2 0                          ##STR50##  R,S    25.313    C.sub.12 H.sub.25        ##STR51##    1 1                          ##STR52##  S,S    27.714    C.sub.9 H.sub.19        ##STR53##    1 0                          ##STR54##  S,R    53.0                                               Example 415    C.sub.9 H.sub.19        ##STR55##    1 0                          ##STR56##  S,S    25.816    C.sub.8 H.sub.17        ##STR57##    1 1                          ##STR58##  S,S,S  34.317    C.sub.8 H.sub.17        ##STR59##    1 0                          ##STR60##  S,S    16.518    C.sub.8 H.sub.17 O        ##STR61##    1 0                          ##STR62##  S,S    45.019    C.sub.8 H.sub.17 O        ##STR63##    1 0                          ##STR64##  S,R    29.420    C.sub.8 H.sub.17        ##STR65##    1 0                          ##STR66##  S,S,S  48.121    C.sub.8 H.sub.17        ##STR67##    1 1                          ##STR68##  R,S    35.222    C.sub.8 H.sub.17        ##STR69##    1 0                          ##STR70##  S,S    22.123    C.sub.9 H.sub.19        ##STR71##    1 0                          ##STR72##  S,S    61.024    C.sub.9 H.sub.19        ##STR73##    1 0                          ##STR74##  S,R    25.025    C.sub.8 H.sub.17 O        ##STR75##    1 0                          ##STR76##  S,S,S  74.426    C.sub.5 H.sub.11        ##STR77##    1 0                          ##STR78##  S,S    14.0__________________________________________________________________________
EXAMPLE 5 (Use example 1)

A composition consisting of the following six kinds of achiral compounds and having SC phase was prepared:

______________________________________ ##STR79##                 30 wt. % ##STR80##                 20 wt. % ##STR81##                 10 wt. % ##STR82##                 10 wt. % ##STR83##                 20 wt. % ##STR84##                 10 wt. %______________________________________

The phase transition points of this composition were as follows: ##STR85##

When a compound of sample No. 6 as a compound of the formula (I) of the present invention was added in an amount of 10% by weight to the above composition, SC* phase exhibiting ferroelectric properties within a temperature range of 16° to 50° C. appeared. This composition had a spontaneous polarization value of 9.4 nC/cm2 at 25° C. and a tilt angle of 16.7°. The composition was filled in a cell of 2 μm thickness provided with transparent electrodes each obtained by coating the surface with PVA as an aligning agent and rubbing the resulting surface to subject it to a parallel aligning treatment, followed by placing the resulting cell between two sheets of crossed polarizers and impressing thereto a square wave of ±10 V. As a result, change in the intensity of transmitted light was observed. The response time was sought from the change in the intensity of transmitted light at that time to give 100 μsec at 25° C.

From the foregoing, it is seen that when the compound of the present invention is used, it is possible to impart a spontaneous polarization to an achiral smectic composition and there is obtained a ferroelectric liquid crystal composition which has a high response rate at room temperature.

EXAMPLE 6

A chiral nematic liquid crystal composition, obtained by adding a compound of sample No. 6 in an amount of 1% by weight to ZLI-1132 manufactured by Merck Company was subjected to measurement of its chiral pitch according to Cano wedge method to give 15 μm at 25° C. Further, the temperature-dependency of pitch δP expressed by the formula ##EQU1## was 0.478 when t1 =20° C. and t2 =60° C.

Claims (8)

What we claim is:
1. An optically active compound expressed by the formula ##STR86## wherein R1 represents a linear or branched chain alkyl group or alkoxy group, each of 5 to 12 carbon atoms;
R2 represents ##STR87## wherein R3 represents a linear or branched chain alkyl group, each of 1 to 15 carbon atoms, and when R3 represents a branched chain alkyl group it may be an optically active group, and R4 represents a linear or branched chain alkyl group, each of 1 to 10 carbon atoms, and when R4 represents a branched chain alkyl group, it may be an optically active group, and X' represents F, Cl or Br; ##STR88## is biphenyl or fluoro-substituted biphenyl, l represents an integer of 1 or 2;
m represents 0; and
* indicates an asymmetric carbon atom.
2. A liquid crystal composition comprising at least two components, at least one of which is an optically active compound as set forth in claim 1.
3. A liquid crystal composition according to claim 2, exhibiting a chiral smectic liquid crystal phase.
4. A liquid crystal composition according to claim 2, exhibiting a chiral nematic liquid crystal phase.
5. A liquid crystal display element containing a liquid crystal composition as set forth in claim 2.
6. An optically active compound according to claim 1, wherein ##STR89##
7. An optically active compound according to claim 6, wherein R2 is ##STR90##
8. An optically active compound expressed by the formula ##STR91## wherein R1 represents a linear or branched alkoxy group of 5 to 12 carbon atoms; R2 represents ##STR92## wherein R4 represents a linear or branched chain alkyl group of 1 to 10 carbon atoms; 1 represents an integer of 1 or 2; and * indicates an asymmetric carbon atom.
US07160279 1987-03-04 1988-02-25 Optically active compound having a plurality of asymmetric carbon atoms Expired - Lifetime US4973426A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP62-49796 1987-03-04
JP4979687 1987-03-04

Publications (1)

Publication Number Publication Date
US4973426A true US4973426A (en) 1990-11-27

Family

ID=12841113

Family Applications (1)

Application Number Title Priority Date Filing Date
US07160279 Expired - Lifetime US4973426A (en) 1987-03-04 1988-02-25 Optically active compound having a plurality of asymmetric carbon atoms

Country Status (4)

Country Link
US (1) US4973426A (en)
KR (1) KR950013094B1 (en)
DE (2) DE3872410D1 (en)
EP (1) EP0281424B1 (en)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5047171A (en) * 1987-09-03 1991-09-10 Chisso Corporation Optically active-2,5-diphenylpyridine
US5080827A (en) * 1987-02-16 1992-01-14 Chisso Corporation 1,2-propanediol derivative
WO1992001763A1 (en) * 1990-07-20 1992-02-06 Displaytech, Inc. Ferroelectric liquid crystal compositions containing chiral haloalkoxy tail units
US5106531A (en) * 1989-02-13 1992-04-21 Chisso Corporation Ferroelectric liquid crystal composition
US5116529A (en) * 1988-11-28 1992-05-26 Chisso Corporation Ferroelectric liquid crystal composition and liquid crystal display element
US5118442A (en) * 1989-06-23 1992-06-02 Mitsubishi Petrochemical Co., Ltd. Optically active compound
US5164112A (en) * 1989-07-21 1992-11-17 Chisso Corporation α-hydroxyketone derivatives, liquid crystal compositions containing said derivatives, and liquid crystal devices using said compositions
US5188761A (en) * 1989-04-07 1993-02-23 Chisso Corporation Ferroelectric liquid crystal composition and light switching element comprising the same
US5190691A (en) * 1988-04-06 1993-03-02 Chisso Corporation Ferroelectric liquid crystal composition
US5340497A (en) * 1989-06-06 1994-08-23 Merck Patent Gesellschaft Mit Beschrankter Haftung Fluorophenylpyrimidines
US5389293A (en) * 1988-09-22 1995-02-14 Sumitomo Chemical Company, Limited Optically active benzene derivatives, process for producing the same and liquid-crystalline composition containing said derivatives as liquid-crystalline compound and light switching elements
US5403511A (en) * 1989-02-27 1995-04-04 Matsushita Electric Industrial Co., Ltd. Ferroelectric liquid crystal composition and ferroelectric liquid crystal display device
US5427714A (en) * 1990-05-23 1995-06-27 Chisso Corporation Ferroelectric liquid crystal composition
US6146547A (en) * 1987-02-02 2000-11-14 Chisso Corporation 2-substituted-alkyl ether and liquid crystal composition
US8596024B2 (en) 2007-11-13 2013-12-03 Infinite Edge Technologies, Llc Sealed unit and spacer

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE68904832D1 (en) * 1988-07-19 1993-03-25 Seiko Instr Inc Fluessigkristallverbindung.
DE69024283D1 (en) * 1989-02-17 1996-02-01 Merck Patent Gmbh Liquid crystal media containing fluorinated oligophenyls
DE69012876D1 (en) * 1989-04-25 1994-11-03 Sumitomo Chemical Co Optically active biphenyl derivatives, processes for their preparation, containing as active ingredient liquid crystal composition and liquid crystal element containing them.
JP2893798B2 (en) * 1989-04-25 1999-05-24 住友化学工業株式会社 Optically active biphenyl derivative, its preparation, the liquid crystal composition to make it an active ingredient and a liquid crystal element formed by using the same
JPH0781144B2 (en) * 1989-06-19 1995-08-30 セイコー電子工業株式会社 Ferroelectric liquid crystal element
JP2852544B2 (en) * 1989-11-07 1999-02-03 チッソ株式会社 Ferroelectric liquid crystal composition

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2161808A (en) * 1984-07-12 1986-01-22 Suwa Seikosha Kk Liquid crystalline 2-phenylpyridine derivatives
EP0175591A2 (en) * 1984-09-20 1986-03-26 Canon Kabushiki Kaisha Lactic acid derivative, liquid crystal composition containing same and liquid crystal device
US4592858A (en) * 1984-04-13 1986-06-03 Ajinomoto Company, Inc. Smectic liquid crystal compound and liquid crystal compositions
DE3515373A1 (en) * 1985-04-27 1986-11-06 Merck Patent Gmbh heterocycles Nitrogenous
WO1987005018A2 (en) * 1986-02-17 1987-08-27 MERCK Patent Gesellschaft mit beschränkter Haftung Optically active compounds
WO1987005012A2 (en) * 1986-02-21 1987-08-27 The Secretary Of State For Defence In Her Britanni Liquid crystal compounds, mixtures and devices
EP0255219A2 (en) * 1986-06-09 1988-02-03 Chisso Corporation Omega-substituted, optically active 2-alkanol ester derivatives
US4725688A (en) * 1984-06-07 1988-02-16 Seiko Instruments Inc. Liquid crystal compound
US4744918A (en) * 1984-07-11 1988-05-17 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid crystal phase

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4592858A (en) * 1984-04-13 1986-06-03 Ajinomoto Company, Inc. Smectic liquid crystal compound and liquid crystal compositions
US4725688A (en) * 1984-06-07 1988-02-16 Seiko Instruments Inc. Liquid crystal compound
US4744918A (en) * 1984-07-11 1988-05-17 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid crystal phase
GB2161808A (en) * 1984-07-12 1986-01-22 Suwa Seikosha Kk Liquid crystalline 2-phenylpyridine derivatives
EP0175591A2 (en) * 1984-09-20 1986-03-26 Canon Kabushiki Kaisha Lactic acid derivative, liquid crystal composition containing same and liquid crystal device
DE3515373A1 (en) * 1985-04-27 1986-11-06 Merck Patent Gmbh heterocycles Nitrogenous
WO1987005018A2 (en) * 1986-02-17 1987-08-27 MERCK Patent Gesellschaft mit beschränkter Haftung Optically active compounds
WO1987005012A2 (en) * 1986-02-21 1987-08-27 The Secretary Of State For Defence In Her Britanni Liquid crystal compounds, mixtures and devices
EP0255219A2 (en) * 1986-06-09 1988-02-03 Chisso Corporation Omega-substituted, optically active 2-alkanol ester derivatives

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6146547A (en) * 1987-02-02 2000-11-14 Chisso Corporation 2-substituted-alkyl ether and liquid crystal composition
US5080827A (en) * 1987-02-16 1992-01-14 Chisso Corporation 1,2-propanediol derivative
US5047171A (en) * 1987-09-03 1991-09-10 Chisso Corporation Optically active-2,5-diphenylpyridine
US5167855A (en) * 1988-03-04 1992-12-01 University Research Corporation Ferroelectric liquid crystal compositions chiral haloalkoxy tail units
US5190691A (en) * 1988-04-06 1993-03-02 Chisso Corporation Ferroelectric liquid crystal composition
US5389293A (en) * 1988-09-22 1995-02-14 Sumitomo Chemical Company, Limited Optically active benzene derivatives, process for producing the same and liquid-crystalline composition containing said derivatives as liquid-crystalline compound and light switching elements
US5693251A (en) * 1988-09-22 1997-12-02 Sumitomo Chemical Company, Limited Optically active benzene derivatives, process for producing the same and liquid-crystalline composition containing said derivatives as liquid-crystalline compound and light switching elements
US5116529A (en) * 1988-11-28 1992-05-26 Chisso Corporation Ferroelectric liquid crystal composition and liquid crystal display element
US5106531A (en) * 1989-02-13 1992-04-21 Chisso Corporation Ferroelectric liquid crystal composition
US5403511A (en) * 1989-02-27 1995-04-04 Matsushita Electric Industrial Co., Ltd. Ferroelectric liquid crystal composition and ferroelectric liquid crystal display device
US5188761A (en) * 1989-04-07 1993-02-23 Chisso Corporation Ferroelectric liquid crystal composition and light switching element comprising the same
US5340497A (en) * 1989-06-06 1994-08-23 Merck Patent Gesellschaft Mit Beschrankter Haftung Fluorophenylpyrimidines
US5118442A (en) * 1989-06-23 1992-06-02 Mitsubishi Petrochemical Co., Ltd. Optically active compound
US5164112A (en) * 1989-07-21 1992-11-17 Chisso Corporation α-hydroxyketone derivatives, liquid crystal compositions containing said derivatives, and liquid crystal devices using said compositions
US5427714A (en) * 1990-05-23 1995-06-27 Chisso Corporation Ferroelectric liquid crystal composition
WO1992001763A1 (en) * 1990-07-20 1992-02-06 Displaytech, Inc. Ferroelectric liquid crystal compositions containing chiral haloalkoxy tail units
US8596024B2 (en) 2007-11-13 2013-12-03 Infinite Edge Technologies, Llc Sealed unit and spacer

Also Published As

Publication number Publication date Type
DE3872410D1 (en) 1992-08-06 grant
KR950013094B1 (en) 1995-10-24 grant
DE3872410T2 (en) 1992-12-03 grant
EP0281424B1 (en) 1992-07-01 grant
EP0281424A1 (en) 1988-09-07 application

Similar Documents

Publication Publication Date Title
US5780629A (en) Polymerizable, chiral compounds and their use
US4613209A (en) Smectic liquid crystals
US4818428A (en) Liquid crystal phase
US4780241A (en) Ferroelectric chiral smectic liquid crystal composition
US4589996A (en) Liquid crystalline carbonic acid esters and liquid crystal compositions containing the same
US4780242A (en) Halogen-containing, optically active liquid crystal compound and liquid crystal composition containing same
Dabrowski et al. Mesomorphic characteristics of some new homologous series with the isothiocyanato terminal group
US4273929A (en) Heterocyclic compounds
US4732699A (en) Biphenyl carbonic acid ester compounds and liquid crystal composition containing the same
US4512636A (en) Liquid crystal compounds
US4911863A (en) Alkylbyphenyloxyacetic acid esters and their use in smectic liquid crystal materials
US20040124399A1 (en) Fluorinated aromatic compounds and the use of the same in liquid crystal mixtures
US4723005A (en) Anisotropic compounds and liquid crystal mixtures
US4664840A (en) Liquid crystal compounds
EP0256636A2 (en) Biphenylyl ethanes and their use in liquid crystal materials and devices
US4614609A (en) Liquid crystalline biphenyl derivatives and mixtures thereof
US4765924A (en) Halogen-containing heterocyclic compound and liquid crystal composition
US4876027A (en) Optically active composition, mesomorphic compound and liquid crystal device
US5482650A (en) Liquid crystal compounds having perfluoroether terminal portions
US4886621A (en) Liquid crystal phase
US4533488A (en) Pyrimidine derivatives
US4349452A (en) Cyclohexylcyclohexanoates
US4482472A (en) Liquid crystal materials
US4820839A (en) Nitrogen-containing heterocyclic esters
EP0325796A1 (en) A liquid crystal compound and a mixture containing the same

Legal Events

Date Code Title Description
AS Assignment

Owner name: CHISSO CORPORATION, 6-32, NAKANOSHIMA 3-CHOME, KIT

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:OHNO, KOUJI;SAITO, SHINICHI;INOUE, HIROMICHI;AND OTHERS;REEL/FRAME:004877/0318

Effective date: 19880210

Owner name: CHISSO CORPORATION, JAPAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:OHNO, KOUJI;SAITO, SHINICHI;INOUE, HIROMICHI;AND OTHERS;REEL/FRAME:004877/0318

Effective date: 19880210

FPAY Fee payment

Year of fee payment: 4

FPAY Fee payment

Year of fee payment: 8

FPAY Fee payment

Year of fee payment: 12